PL448580A1 - 2-(3-Hydroxy-4-nitrobenzoyl)-N-[(naphth-1-yl)methyl]hydrazinecarbothioamide, method of its production and its first medical application - Google Patents

2-(3-Hydroxy-4-nitrobenzoyl)-N-[(naphth-1-yl)methyl]hydrazinecarbothioamide, method of its production and its first medical application

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Publication number
PL448580A1
PL448580A1 PL448580A PL44858024A PL448580A1 PL 448580 A1 PL448580 A1 PL 448580A1 PL 448580 A PL448580 A PL 448580A PL 44858024 A PL44858024 A PL 44858024A PL 448580 A1 PL448580 A1 PL 448580A1
Authority
PL
Poland
Prior art keywords
reaction
hydrazinecarbothioamide
hydroxy
naphth
nitrobenzoyl
Prior art date
Application number
PL448580A
Other languages
Polish (pl)
Other versions
PL247926B1 (en
Inventor
Jolanta Łuniewska-Bury
Mariola Głowacka
Original Assignee
Akademia Mazowiecka W Płocku
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Akademia Mazowiecka W Płocku filed Critical Akademia Mazowiecka W Płocku
Priority to PL448580A priority Critical patent/PL247926B1/en
Publication of PL448580A1 publication Critical patent/PL448580A1/en
Publication of PL247926B1 publication Critical patent/PL247926B1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C337/00—Derivatives of thiocarbonic acids containing functional groups covered by groups C07C333/00 or C07C335/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
    • C07C337/06—Compounds containing any of the groups, e.g. thiosemicarbazides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Przedmiotem zgłoszenia jest nowa pochodna hydrazynokarbotioamidu, o wzorze ogólnym 1 przedstawionym na rysunku, będąca jednoczesnym inhibitorem ludzkiej topoizomerazy II oraz tyrozynazy, która ma zastosowanie w leczeniu czerniaka. Zgłoszenie obejmuje także sposób wytwarzania nowej pochodnej hydrazynokarbotioamidu o wzorze ogólnym 1, że hydrazyd kwasu 3-hydroksy-4-nitrobenzoesowego poddaje się reakcji z izotiocyjanianem 1-naftylometylu, prowadząc reakcję w rozpuszczalnikach organicznych, gdzie postęp reakcji kontroluje się przy użyciu technik chromatograficznych, a po zakończeniu reakcji mieszaninę reakcyjną ochładza się, powstały osad odsącza, suszy a następnie krystalizuje z rozpuszczalników polarnych. Co ważne reakcję w rozpuszczalnikach organicznych prowadzi się we wrzącym etanolu, korzystnie w czasie przez 5 — 30 minut, a otrzymany produkt reakcji krystalizuje się z etanolu.The subject of the application is a new hydrazinecarbothioamide derivative, of general formula 1 shown in the drawing, which is a simultaneous inhibitor of human topoisomerase II and tyrosinase, which is used in the treatment of melanoma. The application also covers a method of producing a new hydrazinecarbothioamide derivative of general formula 1, wherein 3-hydroxy-4-nitrobenzoic acid hydrazide is reacted with 1-naphthylmethyl isothiocyanate, carrying out the reaction in organic solvents, where the progress of the reaction is controlled using chromatographic techniques, and after the reaction is completed, the reaction mixture is cooled, the resulting precipitate is filtered off, dried and then crystallized from polar solvents. Importantly, the reaction in organic solvents is carried out in boiling ethanol, preferably for 5-30 minutes, and the obtained reaction product is crystallized from ethanol.

PL448580A 2024-05-15 2024-05-15 2-(3-Hydroxy-4-nitrobenzoyl)-N-[(naphth-1-yl)methyl]hydrazinecarbothioamide, method of its production and its first medical application PL247926B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PL448580A PL247926B1 (en) 2024-05-15 2024-05-15 2-(3-Hydroxy-4-nitrobenzoyl)-N-[(naphth-1-yl)methyl]hydrazinecarbothioamide, method of its production and its first medical application

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PL448580A PL247926B1 (en) 2024-05-15 2024-05-15 2-(3-Hydroxy-4-nitrobenzoyl)-N-[(naphth-1-yl)methyl]hydrazinecarbothioamide, method of its production and its first medical application

Publications (2)

Publication Number Publication Date
PL448580A1 true PL448580A1 (en) 2024-12-02
PL247926B1 PL247926B1 (en) 2025-09-15

Family

ID=93706939

Family Applications (1)

Application Number Title Priority Date Filing Date
PL448580A PL247926B1 (en) 2024-05-15 2024-05-15 2-(3-Hydroxy-4-nitrobenzoyl)-N-[(naphth-1-yl)methyl]hydrazinecarbothioamide, method of its production and its first medical application

Country Status (1)

Country Link
PL (1) PL247926B1 (en)

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
GOOGLE; A. Szopa et al., Evaluation of developmental toxicity in zebrafish embryos and antiproliferative potential against human tumor cell lines of new derivatives containing 4-nitrophenyl group. Toxicol Appl Pharmacol. 2023 Jan; 458: 116325 *
GOOGLE; Y M. Wos et al., Novel thiosemicarbazide derivatives with 4-nitrophenyl group as multi-target drugs: α-glucosidase inhibitors with antibacterial and antiproliferative activity. Biomed Pharmacother. 2017; 93: 1269-1276 *
GOOGLE; Y P. Kozyra et al., Potential Anticancer Agents against Melanoma Cells Based on an As-Synthesized Thiosemicarbazide Derivative. Biomolecules. 2022; 12(2):151 *

Also Published As

Publication number Publication date
PL247926B1 (en) 2025-09-15

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